Isopropanol → 5-Bromo-2-isopropoxybenzotrifluoride

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-propanol (1.997 mL) in dry tetrahydrofuran (THF) (50 mL) under nitrogen was added potassium tert-butoxide (3.49 g). The reaction mixture was heated to 50° C. for 10 min, then 4-bromo-1-fluoro-2-(trifluoromethyl)benzene (D40) (6.3 g) was added. The resulting mixture was stirred at 50° C. overnight. After cooling the reaction, the solvent was removed in vacuo, the residue was diluted with ethyl acetate (100 mL), washed with water, the organic phase was dried over sodium sulphate, concentrated and the residue was purified by column chromatography to give 4-bromo-1-[(1-methylethyl)oxy]-2-(trifluoromethyl)benzene (D41) (5.21 g) as a clear oil. δH (CDCl3, 600 MHz): 1.36 (6H, d), 4.60 (1H, m), 6.88 (1H, d), 7.55 (1H, dd), 7.66 (1H, d).

Provenance & Evidence